616202-81-4

Usage

Uses

Used in Pharmaceutical Research and Development:
1H-3-Benzazepine, 8-chloro-2,3,4,5-tetrahydro-1-methyl-, (1S)is used as a potential candidate for the development of new drugs due to its pharmacological properties. Its benzazepine structure is known to have diverse biological activities, including antipsychotic and anticonvulsant effects. The presence of a chloro and methyl group may further enhance its therapeutic potential, making it a valuable compound for research in the pharmaceutical industry.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 1H-3-Benzazepine, 8-chloro-2,3,4,5-tetrahydro-1-methyl-, (1S)is used for the synthesis of novel compounds with potential therapeutic applications. Its unique structure and functional groups can be modified to create new molecules with improved pharmacological profiles, such as increased potency, selectivity, or reduced side effects.
Used in Drug Design and Optimization:
1H-3-Benzazepine, 8-chloro-2,3,4,5-tetrahydro-1-methyl-, (1S)serves as a starting point for drug design and optimization efforts. Its structural features can be leveraged to develop new molecules with optimized pharmacokinetic and pharmacodynamic properties, ultimately leading to the discovery of more effective and safer drugs for various therapeutic indications.
Used in Neuropharmacology:
In neuropharmacology, 1H-3-Benzazepine, 8-chloro-2,3,4,5-tetrahydro-1-methyl-, (1S)is used for the investigation of its potential as an antipsychotic or anticonvulsant agent. Its benzazepine backbone and functional groups may interact with specific neurotransmitter receptors or ion channels, modulating neuronal activity and offering new treatment options for neurological disorders.
Used in Drug Discovery:
1H-3-Benzazepine, 8-chloro-2,3,4,5-tetrahydro-1-methyl-, (1S)is utilized in drug discovery processes to identify new lead compounds with therapeutic potential. Its unique structure and stereochemistry can be explored through high-throughput screening and computational methods to find novel molecules with desirable pharmacological properties, accelerating the drug development process.

Upstream product

• 616201-80-0 (+/-)-Lorcaserin 
• 34164-14-2 N-(4-chlorophenylethyl)-2-chloropropanamide 
• 156-41-2 4-chlorophenylethylamine 
• 824430-77-5 8-chloro-1-methyl-4,5-dihydro-1H-benzo[d]azepin-2(3H)-one 
• 616202-78-9 (1S)-N-trifluoroacetyl-8-chloro-2,3,4,5-tetrahydro-1-methyl-1H-3-benzazepine 

Downstream Products

• 851477-54-8 (S)-N-tert-butoxycarbonyl-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine 
• 616201-80-0 (+/-)-Lorcaserin 
• 846589-98-8 Lorcaserin hydrochloride 
• 824430-78-6 (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine L-(+)-tartrate 
• 851477-71-9 (S)-N-trifluoroacetyl-8-chloro-7-iodo-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine 

Relevant academic research and scientific papers

Synthesis of 3-Benzazepines by Metal-Free Oxidative C–H Bond Functionalization–Ring Expansion Tandem Reaction

A metal-free synthesis of biologically important benzazepines is achieved through a single synthetic operation involving an oxidative C–H bond functionalization and ring expansion with diazomethanes as key reagent. This represents a new, strong methodology for the straightforward construction of the seven-ring N-heterocyclic structures under mild conditions using a 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO) oxoammonium salt as oxidant. Moderate to good yields are achieved from simple, readily available tetrahydroisoquinolines, and this methodology has been further successfully applied for the synthesis of the 3-benzazepine drug Lorcaserin. A possible mechanistic pathway for the ring expansion step, comprising the extrusion of nitrogen in a concerted asynchronic process, is proposed based on both mechanistic proof and density function theory (DFT) calculations. (Figure presented.).

Discovery and structure-activity relationship of (1R)-8-chloro-2,3,4,5- tetrahydro-1-methyl-1H-3-benzazepine (Lorcaserin), a selective serotonin 5-HT2C receptor agonist for the treatment of obesity

The synthesis and SAR of a novel 3-benzazepine series of 5-HT2C agonists is described. Compound 7d (lorcaserin, APD356) was identified as one of the more potent and selective compounds in vitro (pEC50 values in functional assays measuring [3H]phosphoinositol turnover: 5-HT 2C = 8.1; 5-HT2A = 6.8; 5-HT2B = 6.1) and was potent in an acute in vivo rat food intake model upon oral administration (ED50 at 6 h = 18 mg/kg). Lorcaserin was further characterized in a single-dose pharmacokinetic study in rat (t1/2 = 3.7 h; F = 86%) and a 28-day model of weight gain in growing Sprague-Dawley rat (8.5% decrease in weight gain observed at 36 mg/kg b.i.d.). Lorcaserin was selected for further evaluation in clinical trials for the treatment of obesity.

Discovery and SAR of new benzazepines as potent and selective 5-HT 2C receptor agonists for the treatment of obesity

We report on the synthesis, biological evaluation and structure-activity relationships for a series of 3-benzazepine derivatives as 5-HT2C receptor agonists. The compounds were evaluated in functional assays measuring [3H] phosphoinositol turnover in HEK-293 cells transiently transfected with h5-HT2C, h5-HT2A or h5-HT2B receptors. Several compounds are shown to be potent and selective 5-HT 2C receptor agonists, which decrease food intake in a rat feeding model.

BENZAZEPINE DERIVATIVES AND METHODS OF PROPHYLAXIS OR TREATMENT OF 5HT2C RECEPTOR ASSOCIATED DISEASES

The present invention relates to substituted-2,3,4,5-tetrahydro-3-benzazepine derivatives that are modulators of the 5HT2C receptor. Accordingly, compounds of the present invention are useful for the prophylaxis or treatment of 5HT2C receptor associated diseases, conditions or disorders, such as, obesity and related disorders.

BENZAZEPINE DERIVATIVES AND METHODS OF PROPHYLAXIS OR TREATMENT OF 5HT2C RECEPTOR ASSOCIATED DISEASES

The present invention relates to substituted-2,3,4,5-tetrahydro-3-benzazepine derivatives that are modulators of the 5HT2C receptor. Accordingly, compounds of the present invention are useful for the prophylaxis treatment of 5HT2C receptor associated diseases, conditions or disorders, such as, obesity and related disorders.